20466-07-3

Basic information

• Product Name: 1-phenylpentacyclo[6.6.6.0~2,7~.0~9,14~.0~15,20~]icosa-2,4,6,9,11,13,15,17,19-nonaene (non-preferred name)
• Synonyms: 9-phenyl-9,10-dihydro-9,10-[1,2]benzenoanthracene;9,10[1',2']-Benzenoanthracene, 9,10-dihydro-9-phenyl-
• CAS NO: 20466-07-3
• Molecular Formula: C₂₆H₁₈
• Molecular Weight: 330.4211
• Mol File: 20466-07-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 432.5°C at 760 mmHg
• Flash Point: 212.4°C
• Density: 1.217g/cm³
• Vapor Pressure: 2.8E-07mmHg at 25°C
• Refractive Index: 1.704
• CAS DataBase Reference: 1-phenylpentacyclo[6.6.6.0~2,7~.0~9,14~.0~15,20~]icosa-2,4,6,9,11,13,15,17,19-nonaene (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylpentacyclo[6.6.6.0~2,7~.0~9,14~.0~15,20~]icosa-2,4,6,9,11,13,15,17,19-nonaene (non-preferred name)(20466-07-3)
• EPA Substance Registry System: 1-phenylpentacyclo[6.6.6.0~2,7~.0~9,14~.0~15,20~]icosa-2,4,6,9,11,13,15,17,19-nonaene (non-preferred name)(20466-07-3)

Safety Data

• Hazardous Substances Data: 20466-07-3(Hazardous Substances Data)

Usage

Molecular structure

A phenyl group attached to a polycyclic hydrocarbon ring system with five cyclohexane rings connected in a non-linear arrangement.

Carbon atoms

The compound contains a total of 20 carbon atoms.

Reactivity

The presence of multiple double bonds leads to high reactivity.

Organic synthesis

Due to its reactivity, the compound has potential usefulness in organic synthesis.

Upstream product

• 591-50-4 iodobenzene 
• 602-55-1 9-phenylanthracene 
• 4661-46-5 2-carboxybenzene diazonium chloride 

Downstream Products

• 1394839-44-1 (η⁶-(9-Phenyl)-1,2,3,4,4a,9a-triptycene)tricarbonylchromium 

Relevant articles and documents

Organocopper cross-coupling reaction for C-C bond formation on highly sterically hindered structures

We describe a powerful, broadly applicable cross-coupling protocol that enables carbon-carbon bond formation at highly sterically hindered carbon centers (both sp2 and sp3) by employing organocopper reagents under palladium catalysis. Experimental studies and theoretical calculations indicated that the key to the unique reactivity of copper is the relatively low activation energy of the compact transmetalation transition state, due to Cu(i)-Pd(ii) interaction, which is associated with small values of deformation energy of the reactants. This reaction is applicable to a variety of bulky substrates, including compounds inert to previous cross-coupling chemistry and has high functional group tolerance.